4-bromo-1H-indole-2-carboxylic acid → 4-(2-Ethylphenyl)-indole-2-carboxylic acid

HRID 2355782Notes

Reaction equation

HRID 2355782 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]2.[CH2:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O)[CH3:15]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]2)[CH3:15]

Participants

6

Reactant 2

HCID 40426044-bromo-1H-indole-2-carboxylic acidHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 442331804-(2-Ethylphenyl)-indole-2-carboxylic acid

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 0.28 g of 4-bromo-indole-2-carboxylic acid and 0.069 g of tetrakistriphenylphosphinepalladium in 11 ml of toluene and 2 ml of 2M soda is added a solution of 0.300 g of 2-ethylphenylboronic acid in 3 ml of ethanol. This mixture is refluxed for 16 h, filtered and the aqueous phase acidified with 2N HCl and extracted with ethyl acetate. Concentration of the organic phase gives the product as a brownish powder, m.p. 230-233°, sufficiently pure for the next step.

Workup

  1. temperatureThis mixture is refluxed for 16 h
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-5eef3d9a6b8b41cf95a6131fb2ec8abd
Source dataset
uspto-grants-2010_07
Patent number
US07754896B2

Reaction notes

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